Regioselectivity and kinetics of fluorination of alkyl substituted phenolsby N-fluoro-1,4-diazoniabicyclo[2.2.2]octane salt analogues

Arkivoc

Volumn 2003, Issue 14, 2003, Pages 187-197

  Jereb, Marjan ^a   Zupan, Marko ^a   Stavber, Stojan ^a  

^a UNIVERSITY OF LJUBLJANA   (Slovenia)

Author keywords

Accufluor; Fluorination; Kinetics; Phenols; Selectfluor

Indexed keywords

1 FLUORO 4 CHLOROMETHYL 1,4 DIAZONIABICYCLO[2.2.2]OCTANE BIS TETRAFLUOROBORATE; 1 FLUORO 4 HYDROXY 1,4 DIAZONIABICYCLO[2.2.2]OCTANE BIS TETRAFLUOROBORATE; 3,4 XYLENOL; 5 INDANOL; 5,6,7,8 TETRAHYDRO 2 NAPHTHOL; DIAZONIUM COMPOUND; NAPHTHOL DERIVATIVE; OCTANE; PHENOL DERIVATIVE; SOLVENT; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; ELIMINATION REACTION; FLUORINATION; KINETICS; REACTION ANALYSIS; SUBSTITUTION REACTION; THERMODYNAMICS;

EID: 3242663558     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (27)

1. (a) Lal, G.S.; Pez, G.P.; Syvret, R.G. Chem. Rev. 1996, 96, 1737;
2. (b). Taylor, S.D.; Kotoris, C.C.; Hum, G. Tetrahedron 1999, 55, 12431;
3. (c) Furin, G.G.; Fainzilberg, A.A. Russian Chem. Rev. 1999, 68, 653.
4. (a) Baasner, B.; Hagemann, H.; Tatlow, J.C. (eds) Methods of Organic Chemistry (Houben-Weyl) Vol. E 10a and 10b: Organofluorine Compounds, Thieme: New York, 1999;
5. (b) Hudlicky, M., Pavlath, A.E. eds. Chemistry of Organic Fluorine Compounds II. A Critical Review. ACS Monograph 187. ACS: Washington DC, 1995;
6. (c) Hiyama T. Organofluorine Compounds. Chemistry and Applications. Springer-Verlag: Berlin, 2000.
7. (a) Banks, R.E.; Mohialdin-Khaffaf, S.N.; Lal, S.G.; Sharif, I.; Syvret, R.G. J. Chem. Soc., Chem. Commun. 1992, 595;
8. (b) Stavber, S.; Zupan, M.; Poss, A.J.; Shia, G.A. Tetrahedron Lett. 1995, 36, 6769;
9. (c) Umemoto, T.; Nagayoshi, M. Bull. Chem. Soc. Jpn. 1996, 69, 2287.
10. (a) Gilicinski, A.G.; Pez, G.P.; Syvret, R.G.; Lal, G.S. J. Fluorine Chem. 1992, 59, 157;
11. (b) Differding, E.; Bersier, P.M. Tetrahedron 1992, 48, 1595.
12. Girina, G.P.; Faizil'berg, A.A.; Feoktistov, L.G. Russ. J. Electrochem. 2000, 36, 162.
13. (a) Zupan, M.; Iskra, J.; Stavber, S. Bull. Chem. Soc. Jpn. 1995, 68, 1655;
14. (b) Stavber, S.; Zupan, M. Synlett 1996, 693;
15. (c) Stavber, S.; Jereb, M.; Zupan, M. Synlett 1999, 1375;
16. (d) Stavber, S.; Jereb, M.; Zupan, M. Arkivoc 2001, (V), 98; htpp://www.arkat-usa.org/ark/journal/volume2/part3/Tisler/MT-160B/MT-160B.pdf;
17. (e) Stavber, S.; Jereb, M.; Zupan, M. J. Phys. Org. Chem. 2002, 15, 56.
18. Mills, W.H.; Nixon, I.G. J. Chem. Soc. 1930, 2510.
19. (a) Nilsson, J.L.G.; Selander, H.; Sievertsson, H.; Skanberg, I.; Svensson, K.G. Acta Chim. Scand. 1971, 25, 94;
20. (b) Tee, S.O.; Iyegar, N.R.; Bennett, J.M. J. Org. Chem. 1986, 51, 2585.
21. (a) Bergquist, K.E.; Nilsson, A.; Ronlan, A. Acta Chim. Scand. 1982, 36, 675;
22. (b) Nilsson, A.; Ronlan, A.; Parker, V.D. Tetrahedron Lett. 1975, 16, 1107;
23. (c) Ferron, B.; Jacquesy, J.C.; Jouannetaud, M.P.; Karam, O.; Coustard, J.M. Tetrahedron Lett. 1993, 34, 2949.
24. (a) Meuers, J.H.H.; Sopher, D.W.; Eilenberg, W. Angew. Chem. 1989, 101, 955;
25. (b) Karam, O.; Jacquesy, J.C.; Jouannetaud, M.P. Tetrahedron Lett. 1994, 35, 2541.
26. Kikimuto, R.; Tobe, A.; Fukami, H.; Egawa, M. J. Med .Chem. 1983, 26, 246.
27. Vaughan, J.; Wright, J.G. J. Org. Chem. 1968, 33, 2580.